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Record Information
Version1.0
Creation Date2016-09-30 22:20:21 UTC
Update Date2020-06-04 22:07:36 UTC
MCDB ID BMDB0000161
Secondary Accession Numbers
  • BMDB00161
Metabolite Identification
Common NameL-Alanine
DescriptionL-Alanine, also known as (S)-alanine or L-alpha-alanine, belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Alanine is a drug which is used for protein synthesis. L-Alanine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Alanine exists in all living species, ranging from bacteria to humans. L-Alanine is a potentially toxic compound. L-Alanine has been found to be associated with several diseases known as eosinophilic esophagitis, late-onset preeclampsia, autism, and perillyl alcohol administration for cancer treatment; also l-alanine has been linked to the inborn metabolic disorders including glucagon deficiency.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-Aminopropanoic acidChEBI
(S)-2-Aminopropanoic acidChEBI
(S)-AlanineChEBI
AChEBI
AlaChEBI
ALANINEChEBI
L-2-Aminopropionic acidChEBI
L-AlaninChEBI
L-alpha-AlanineChEBI
(2S)-2-AminopropanoateGenerator
(S)-2-AminopropanoateGenerator
L-2-AminopropionateGenerator
L-a-AlanineGenerator
L-Α-alanineGenerator
(S)-(+)-AlanineHMDB
(S)-2-Amino-propanoateHMDB
(S)-2-Amino-propanoic acidHMDB
2-AminopropanoateHMDB
2-Aminopropanoic acidHMDB
2-AminopropionateHMDB
2-Aminopropionic acidHMDB
2-AmmoniopropanoateHMDB
2-Ammoniopropanoic acidHMDB
a-AlanineHMDB
a-AminopropionateHMDB
a-Aminopropionic acidHMDB
alpha-AlanineHMDB
alpha-AminopropanoateHMDB
alpha-Aminopropanoic acidHMDB
alpha-AminopropionateHMDB
alpha-Aminopropionic acidHMDB
L-(+)-AlanineHMDB
L-2-AminopropanoateHMDB
L-2-Aminopropanoic acidHMDB
L-a-AminopropionateHMDB
L-a-Aminopropionic acidHMDB
L-alpha-AminopropionateHMDB
L-alpha-Aminopropionic acidHMDB
AbufèneHMDB
Alanine doms-adrian brandHMDB
Alanine, L-isomerHMDB
Doms-adrian brand OF alanineHMDB
Doms adrian brand OF alanineHMDB
L-Isomer alanineHMDB
Alanine, L isomerHMDB
L AlanineHMDB
Chemical FormulaC3H7NO2
Average Molecular Weight89.0932
Monoisotopic Molecular Weight89.047678473
IUPAC Name(2S)-2-aminopropanoic acid
Traditional NameL-alanine
CAS Registry Number56-41-7
SMILES
C[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
InChI KeyQNAYBMKLOCPYGJ-REOHCLBHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlanine and derivatives
Alternative Parents
Substituents
  • Alanine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point300 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility204 mg/mLHuman Metabolome Project
LogP-2.85SANGSTER (1994)
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-2.8ChemAxon
logS0.7ALOGPS
pKa (Strongest Acidic)2.47ChemAxon
pKa (Strongest Basic)9.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.5 m³·mol⁻¹ChemAxon
Polarizability8.49 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-014i-0900000000-c7f6dbace291e8305a4e2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014i-0900000000-381ddf4d9ea77be0b8a52014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-01b9-6900000000-6a7c1bb2915e5dd0791f2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-1900000000-84b389f82562c29a81482014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00kf-9000000000-b2f7507be509a85d821b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0900000000-941672891ab94cf5015d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0f79-0910000000-47bd3e3aa274a653a64e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-c7f6dbace291e8305a4e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0900000000-381ddf4d9ea77be0b8a52017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0a4i-1940000000-5def9f7c902aaf1ef6072017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01b9-6900000000-6a7c1bb2915e5dd0791f2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1900000000-84b389f82562c29a81482017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-d31f7a2ed8284a740b592016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9100000000-ab365202f52df8e6d4012017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-9000000000-55d0139f513946f764612012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9000000000-5b0dff13a98daf7822052012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-000i-9000000000-37db595fcf7364600bc92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-55d0139f513946f764612017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-5b0dff13a98daf7822052017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9000000000-37db595fcf7364600bc92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-000i-9000000000-9ca90486c916f938450b2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-e9e9900761fdd599ee3f2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-17dcfdd88dc79713c4b72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-8cc23f8c1455fdf68df52021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9000000000-7b5177095a55ce6895652021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 33V, Negativesplash10-0uxr-9400000000-b26be1c8f3385f90fcc32021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 33V, Negativesplash10-02ti-9000000000-41eecbbaba19b8b0b5362021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9000000000-96b54b269c91ab21be082012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-a8008305399aa1097e1a2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-7253c912562200edc2312012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-00kf-9000000000-72694f3a1a5de3b497902012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-9000000000-5129e160acf979ac549e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-11c20eba8c5ad41d806c2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0006-9000000000-df7c7d6a6ae2d6bccefe2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-324772442476131822142012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-000f-9002000000-4873ce0cdcac54d681862012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0006-9000000000-8193842b36c819ca3ec62012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-fefc31c264a2f0fcf6d02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-ba42bcd60aa9182a780e2017-09-14View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected and Quantified29 - 78 uM details
Detected and Quantified9 - 91 uM details
Detected and Quantified13469 uM details
Detected and Quantified13469 uM details
Detected and Quantified13469 uM details
Detected and Quantified13469 uM details
Detected and Quantified12346 uM details
Detected and Quantified12346 uM details
Detected and Quantified12346 uM details
Detected and Quantified32 +/- 3 uM details
Detected and Quantified33 +/- 2 uM details
Detected and Quantified32 +/- 1 uM details
Detected and Quantified34 +/- 3 uM details
Detected and Quantified29 +/- 2 uM details
Detected and Quantified33 +/- 1 uM details
Detected and Quantified31 +/- 1 uM details
Detected and Quantified31 +/- 3 uM details
Detected and Quantified28 +/- 6 uM details
Detected and Quantified24 +/- 5.4 uM details
Detected and Quantified29 +/- 5.91 uM details
HMDB IDHMDB0000161
DrugBank IDDB00160
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000556
KNApSAcK IDC00001332
Chemspider ID5735
KEGG Compound IDC00041
BioCyc IDL-ALPHA-ALANINE
BiGG ID33629
Wikipedia LinkAlanine
METLIN IDNot Available
PubChem Compound5950
PDB IDNot Available
ChEBI ID16977
References
Synthesis ReferenceChibata I; Kakimoto T; Kato J Enzymatic production of L-alanine by Pseudomonas dacunhae. Applied microbiology (1965), 13(5), 638-45.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
  2. Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
  3. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  4. Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
  5. Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
  6. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
  7. Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
  8. Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]
  9. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  10. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  11. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  12. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  13. Fooddata+, The Technical University of Denmark (DTU) [Link]